February 22, 2009: Clinton possibly talks on an unsecure phone line after experiencing technical trouble.

At 6:39 p.m., Clinton emails her chief of staff Cheryl Mills, saying she just arrived home from a trip to Asia and wants to talk to her over a secure phone line. However, a back and forth email exchange shows that there is a technical problem with Mills’ secure cell phone.

At almost the exact same time, Mills emails Clinton, “I just spoke to ops [operations] and called you reg [regular] line — we have to wait until we see each other b/c [because the] technology is not working.”

Six minutes later, Clinton replies, “Pls [please] try again.”

The Hill will later note, “It’s unclear whether the two did connect or if they moderated any discussion they may have had to avoid sensitive topics while on an unsecure landline.”